Isopropyl chloroacetate → 1,2-Benzisothiazole-2(3H)-acetic acid, 3-oxo-, 1-methylethyl ester, 1,1-dioxide

HRID 2291647Notes

Reaction equation

HRID 2291647 reaction equation
Cl[CH2:2][C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4].O.O.[Na].[S:12]1([C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16](=[O:17])[NH:15]1)(=[O:14])=[O:13]>CN(C)C=O.O>[O:17]=[C:16]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=2[S:12](=[O:14])(=[O:13])[N:15]1[CH2:2][C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 7759Isopropyl chloroacetateHCID 46942257CID 46942257

Product 1

HCID 45196241,2-Benzisothiazole-2(3H)-acetic acid, 3-oxo-, 1-methylethyl ester, 1,1-dioxideYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

23.3 kg (170.6 mol) of isopropyl chloroacetate are added to a solution at 50° C. of 40 kg (165.8 mol) of saccharin sodium dihydrate in 40 l of dimethylformamide. The mixture is heated to 120° C. and maintained for 3 hours at this temperature. The mixture is cooled and diluted with 240 l of water. Finally, the precipitate is centrifuged, washed with cold water and dried, 40.6 kg (86%) of a crystalline white solid, m.p. 112°-7° C. (118°-9° C. from isopropanol), being obtained.

Workup

  1. temperaturemaintained for 3 hours at this temperature
  2. temperatureThe mixture is cooled
  3. washwashed with cold water
  4. customdried

Sources & evidence

ORD record
ord-41b46a753549454fb63a8d871b97e157
Source dataset
uspto-grants-1989_01
Patent number
US04797483

Reaction notes

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